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Vol. 26 No. 22 (2014): Vol 26 Issue 22

Copyright (c) 2014 AJC

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Synthesis and Antibacterial Activity of Pinanyl-2-amino Pyrimidines

https://doi.org/10.14233/ajchem.2014.17778
Jun Wu
Institute of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Peng-Na Wang
Institute of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Xu Xu
Institute of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China; Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, Nanjing 210037, Jiangsu Province, P.R. China
Yi-Qin Yang
Institute of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Shi-Fa Wang
Institute of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China; Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, Nanjing 210037, Jiangsu Province, P.R. China

Corresponding Author(s) : Shi-Fa Wang

wangshifa65@163.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22

Abstract

A new series of pinene-2-alkyl amino pyrimidines were synthesized from (-)-b-pinene. (+)-No-pinone was obtained from (-)-b-pinene by selective oxidation with potassium permanganate and it was reacted with aromatic aldehydes including benzaldehyde, p-methylbenzaldehyde, p-methoxylbenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde, p-fluorobenzaldehyde, o-chlorobenzaldehyde, m-nitrobenzaldehyde, o-vanillin and furfural catalyzed with alkali catalysts to get optically active 3-arylidenenopinones 2a-2l. Then in the alkali catalytic conditions, they were used to synthesize pinanyl-2-amino pyrimidines (3a-3l) with guanidine hydrochloride. The structures of the synthesized compounds were identified by 1H NMR, 13C NMR, FT-IR, GC-MS and elemental analysis. The antimicrobial activity of the newly synthesized pinanyl-2-amino pyrimidines (3a-3l) was done against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. Subtilis and P. fluorescens. It has been observed that compounds 3a and 3g have strong inhibition effect against Candida albicans, 3g has strong inhibition effect against Aspergillus niger, while 3g also has strong inhibition effect against Candida tropicalis.

Keywords

3-Arylidenenopinones Pinanyl-2-amino pyrimidines (-)-β-Pinene ( )-Nopinone Antibacterial activity
Wu, J., Wang, P.-N., Xu, X., Yang, Y.-Q., & Wang, S.-F. (2014). Synthesis and Antibacterial Activity of Pinanyl-2-amino Pyrimidines. Asian Journal of Chemistry, 26(22), 7769–7775. https://doi.org/10.14233/ajchem.2014.17778
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